75319-63-0

Usage

InChI:InChI=1/C22H44O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-27-22-21(26)20(25)19(24)18(17-23)28-22/h18-26H,2-17H2,1H3/t18-,19-,20+,21-,22-/m1/s1

Upstream product

• 83-87-4 D-glucose pentaacetate 
• 36653-82-4 1-Hexadecanol 
• 92052-29-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 85339-28-2 hexadecyl-2,3,4,6-tetra-O-acetate-β-D-glucopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 50-99-7 D-glucose 
• 54549-27-8 cetyl D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 4163-60-4 β-D-galactose peracetate 
• 85339-28-2 hexadecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Downstream Products

• 17460-02-5 1-O-palmityl-D-glucuronic acid 

Relevant academic research and scientific papers

Hexadecyl-β-D-glucopyranoside: A liquid crystal with surfactant properties for stabilization of microemulsions

Lyotropic liquid crystals (LLC) having amphiphilic properties are promising materials as co-surfactants in emulsion formulations. A carbohydrate lyotropic liquid crystal, hexadecyl-β-D-glucopyranoside, was synthesized by linking D-glucose to cetyl alcohol via acetylated glucoside and its ability to stabilize microemulsions was investigated. The synthesized compound was characterized by using Nuclear Magnetic Resonance Spectroscopy (NMR) and Fourier Transform Infrared Spectroscopy (FTIR). Both acetylated and deacetylated compounds were found to exhibit thermotropic and lyotropic liquid crystal behavior. The critical micelle concentration (CMC) value of 1.53 × 10-5mol dm-3 obtained for hexadecyl-β-D-glucopyranoside from both UV-visible spectroscopic and turbidity methods suggests its non-ionic surfactant properties. Calculated HLB value of 8.86 indicates that it is suitable for making self-emulsifying oils and water in oil (W/O) emulsions. By introducing optimum amount of 0.05 wt% of newly synthesized hexadecyl-β-D-glucopyranoside as a co-surfactant, macro emulsions formulated with olive oil, water and non-ionic lipophilic surfactant sorbitan monostearate (Span 80) was successfully converted into microemulsions.

Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics

A series of 19 synthetic alkyl and thioalkyl glycosides derived from D-mannose, D-glucose and D-galactose and having C10–C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-D-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-D-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.

Polyvalent effect enhances diglycosidic antiplasmodial activity

An efficient and facile total synthesis of diglycoside Matayoside D isolated from the root bark of Matayba guianensis with antiplasmodial activity have been accomplished in 11 steps with 5% overall yields starting from commercially available glucose and rhamnose. Furthermore, a class of the diglycosidic derivatives with different lengths of the linker and valences were also prepared and evaluated for their antiplasmodial activities against chloroquine-susceptible (3D7) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Low valent and short linker attached diglycoside show no enhancement of the antiplasmodial activity while polyvalent conjugates showed enhanced antiplasmodial activity with IC50 value at least 20 fold better than that of the corresponding diglycosidic monomer. The polyvalent diglycoside were non-cytotoxic against normal mammalian cells under 50,000 μg/L.

Design and synthesis of cluster neoglycoconjugates based on D-glucose

Synthetic approaches have been developed to tetravalent neoglycoconjugates with different structures of the hydrophobic fragment and D-glucose fragment as branching core. The syntheses have been accomplished by preparation of blocks with terminal C C triple bonds and hydrophobic fragment and hydrophilic component (lactose derivative), followed by their conjugation.

A novel type of highly effective nonionic gemini Alkyl O-glucoside surfactants: A nersatile strategy of design

A novel type of highly effective gemini alkyl glucosides has been rationally designed and synthesized. The gemini surfactants have been readily prepared by glycosylation of the gemini alkyl chains that are synthesized with regioselective ring-opening of ethylene glycol epoxides by the alkyl alcohols. The new gemini alkyl glucosides exhibit significantly better surface activity than the known results. Then rheological, DLS, and TEM studies have revealed the intriguing self-assembly behavior of the novel gemini surfactants. This study has proved the effectiveness of the design of gemini alkyl glucosides which is modular, extendable, and synthetically simple. The new gemini surfactants have great potential as nano carriers in drug and gene delivery.

The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure α- or β-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested.

Synthesis and biocompatibility evaluation of fluorinated, single-tailed glucopyranoside surfactants

Partially fluorinated non-ionic surfactants are of interest for a range of biomedical applications, such as the pulmonary administration of drugs using reverse water-in-perfluorocarbon microemulsions. We herein report the synthesis and characterization of a series of partially fluorinated β-d- glucopyranoside surfactants from the respective alcohols and peracetylated β-d-glucopyranoside using BF3·Et2O as catalyst. The surfactant packing parameter of the fluorinated surfactants ranged from 0.472 to 0.534 (MOPAC calculations) or 0.562 to 0.585 (calculated from literature values), which is comparable to surfactants with a similar partially fluorinated tail. Based on an initial biocompatibility assessment, the β-d-glucopyranoside surfactants have low toxicities in the B16F10 mouse melanoma cell line and comparatively low haemolytic activities towards rabbit red blood cells. The fluorinated surfactants appear to be less toxic towards cells in culture and to have a lower haemolytic activity compared to their hydrocarbon analogs. Furthermore, an increasing degree of fluorination appears to reduce both the cytotoxicity and the haemolytic activity. Similar structure-activity relationships have been reported for other partially fluorinated surfactants. Overall, these findings suggest that the surfactants may be useful for biomedical applications, such as novel drug delivery systems. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2008.

BF3 etherate-induced formation of C7-C 16-alkyl β-D-glucopyranosides

BF3 etherate-induced formation of C7-C 16-alkyl D-glucopyranosides is used as the key step in their synthesis from glucose and C7-C16-alkanols.

New modified single chained glycolipids. Part 1: Synthesis of deoxy and partially O-methylated glycolipids with or without a sulfur containing spacer

A way to synthesize neoglycolipids with high yields and anomeric purity is described. Starting point of the synthesis strategy is the glycosylation of allyl alcohol with definite steric orientation. Introduction of the hydrophobic moiety was achieved by photoaddition of n-hexadecanethiol and 3-mercaptopropionic acid followed by amidation with n-hexadecylamine, respectively. In order to investigate the influence of different carbohydrate headgroups in the physicochemical behavior of the general glycolipid, especially the orientation of the alkyl chain, a range of neoglycolipids was synthesized. Beside the differences in the configuration between unfunctionalized glycopyranoses like D-glucose, D-galactose and D-mannose, a number of deoxy and partially O-methylated sugar derivatives was prepared. The divergences concerning the different carbohydrate headgroups and the hydrophobic moiety, respectively, can be compared to relatively simple structured glycolipids with hexadecyl residue and without spacer function.

Synthesis of C7-C16-alkyl glycosides: Part III - Synthesis of alkyl D-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (galactose) with fatty alkanols is used in a synthesis of C7-C16-alkyl galactopyranosides. The process occurs under the influence of tin(IV) chloride as a Lewis acid catalyst.